13C- 13C Spin-spin coupling constants in structural studies: XXXVII. Rotational conformations of hydroxy groups in pyranose, furanose, and septanose rings

Russian Journal of Organic Chemistry

Volumn 40, Issue 8, 2004, Pages 1194-1199

  Danilova, V A ^a   Istomina, N V ^a   Krivdin, L B ^a  

^a ANGARSK STATE TECHNICAL UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; FURAN DERIVATIVE; HEPTOSE; HYDROXYL GROUP; MONOSACCHARIDE; PYRAN DERIVATIVE;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL BOND; CONFORMATION; DENSITY FUNCTIONAL THEORY; STRUCTURE ANALYSIS;

EID: 7244234450     PISSN: 10704280     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:RUJO.0000045905.01006.4f     Document Type: Article

References (37)

1. Serianni, A.S., Glycoconjugates: Composition, Structure, and Function, Allen, H.J. and Kisailus, E.C., Eds., New York: Marcel Dekker, 1992, p. 71; Serianni, A.S., NMR of Biological Macromolecules. NATO ASI Series H: Cell Biology, Stassinopoulou, C.I., New York: Springer, 1994, vol. 87, p. 293.
2. Serianni, A.S., Glycoconjugates: Composition, Structure, and Function, Allen, H.J. and Kisailus, E.C., Eds., New York: Marcel Dekker, 1992, p. 71; Serianni, A.S., NMR of Biological Macromolecules. NATO ASI Series H: Cell Biology, Stassinopoulou, C.I., New York: Springer, 1994, vol. 87, p. 293.
3. Krivdin, L.B. and Kalabin, G.A., Prog. NMR Spectrosc., 1989, vol. 21, no. 4/5, p. 293.
4. Marshall, J.L., Carbon-Carbon and Carbon-Proton NMR Couplings: Applications to Organic Stereochemistry and Conformational Analysis, Marchand, A.P., Ed., Deerfield Beach: Chem. Int., 1983; Krivdin, L.B. and Zinchenko, S.V., Curr. Org. Chem., 1998, vol. 2, p. 173; Krivdin, L.B. and Della, E.W., Prog. NMR Spectrosc., 1991, vol. 23, nos. 4-6, p. 301.
5. Marshall, J.L., Carbon-Carbon and Carbon-Proton NMR Couplings: Applications to Organic Stereochemistry and Conformational Analysis, Marchand, A.P., Ed., Deerfield Beach: Chem. Int., 1983; Krivdin, L.B. and Zinchenko, S.V., Curr. Org. Chem., 1998, vol. 2, p. 173; Krivdin, L.B. and Della, E.W., Prog. NMR Spectrosc., 1991, vol. 23, nos. 4-6, p. 301.
6. Marshall, J.L., Carbon-Carbon and Carbon-Proton NMR Couplings: Applications to Organic Stereochemistry and Conformational Analysis, Marchand, A.P., Ed., Deerfield Beach: Chem. Int., 1983; Krivdin, L.B. and Zinchenko, S.V., Curr. Org. Chem., 1998, vol. 2, p. 173; Krivdin, L.B. and Della, E.W., Prog. NMR Spectrosc., 1991, vol. 23, nos. 4-6, p. 301.
7. Wu, J., Bondo, P.B., Vuorinen, T., and Serianni, A.S., J. Am. Chem. Soc., 1992, vol. 114, p. 3499.
8. King-Morris, M.J. and Serianni, A.S., J. Am. Chem. Soc., 1987, vol. 109, p. 3501.
9. Danilova, V.A. and Krivdin, L.B., Russ. J. Org. Chem., 2003, vol. 39, p. 663.
10. Danilova, V.A. and Krivdin, L.B., Russ. J. Org. Chem., 2003, vol. 39, p. 1764.
11. Danilova, V.A. and Krivdin, L.B., Russ. J. Org. Chem., 2004, vol. 40, p. 57.
12. Malkin, V.G., Malkina, O.L., Casida, M.E., and Salahub, D.R., J. Am. Chem. Soc., 1994, vol. 116, p. 5898; Malkin, V.G., Malkina, O.L., Eriksson, L.A., and Salahub, D.R., Modern Density Functional Theory: A Tool for Chemistry. Theoretical and Computional Chemistry, vol. 2, Seminario, J.M. and Politzer, P., Eds., Amsterdam: Elsevier, 1995; Malkina, O.L., Salahub, D.R., and Mal-kin, V.G., J. Chem. Phys., 1996, vol. 105, p. 8793; Mal-kin, V.G., Malkina, O.L., Steinbrunner, G., and Huber, H., Chem. Eur. J., 1996, vol. 2, p. 452.
13. Malkin, V.G., Malkina, O.L., Casida, M.E., and Salahub, D.R., J. Am. Chem. Soc., 1994, vol. 116, p. 5898; Malkin, V.G., Malkina, O.L., Eriksson, L.A., and Salahub, D.R., Modern Density Functional Theory: A Tool for Chemistry. Theoretical and Computional Chemistry, vol. 2, Seminario, J.M. and Politzer, P., Eds., Amsterdam: Elsevier, 1995; Malkina, O.L., Salahub, D.R., and Mal-kin, V.G., J. Chem. Phys., 1996, vol. 105, p. 8793; Mal-kin, V.G., Malkina, O.L., Steinbrunner, G., and Huber, H., Chem. Eur. J., 1996, vol. 2, p. 452.
14. Malkin, V.G., Malkina, O.L., Casida, M.E., and Salahub, D.R., J. Am. Chem. Soc., 1994, vol. 116, p. 5898; Malkin, V.G., Malkina, O.L., Eriksson, L.A., and Salahub, D.R., Modern Density Functional Theory: A Tool for Chemistry. Theoretical and Computional Chemistry, vol. 2, Seminario, J.M. and Politzer, P., Eds., Amsterdam: Elsevier, 1995; Malkina, O.L., Salahub, D.R., and Mal-kin, V.G., J. Chem. Phys., 1996, vol. 105, p. 8793; Mal-kin, V.G., Malkina, O.L., Steinbrunner, G., and Huber, H., Chem. Eur. J., 1996, vol. 2, p. 452.
15. Malkin, V.G., Malkina, O.L., Casida, M.E., and Salahub, D.R., J. Am. Chem. Soc., 1994, vol. 116, p. 5898; Malkin, V.G., Malkina, O.L., Eriksson, L.A., and Salahub, D.R., Modern Density Functional Theory: A Tool for Chemistry. Theoretical and Computional Chemistry, vol. 2, Seminario, J.M. and Politzer, P., Eds., Amsterdam: Elsevier, 1995; Malkina, O.L., Salahub, D.R., and Mal-kin, V.G., J. Chem. Phys., 1996, vol. 105, p. 8793; Mal-kin, V.G., Malkina, O.L., Steinbrunner, G., and Huber, H., Chem. Eur. J., 1996, vol. 2, p. 452.
16. Bose, B., Zhao, S., Stenutz, R., Cloran, F., Bondo, P.B., Bondo, G., Hertz, B., Carmichael, I., and Serianni, A.S., J. Am. Chem. Soc., 1998, vol. 120, p. 11 158; Cloran, F., Carmichael, I., and Serianni, A.S., J. Phys. Chem. A, 1999, vol. 103, p. 3783; Church, T.J., Carmichael, I., and Serianni, A.S., J. Am. Chem. Soc., 1997, vol. 119, p. 8946.
17. Bose, B., Zhao, S., Stenutz, R., Cloran, F., Bondo, P.B., Bondo, G., Hertz, B., Carmichael, I., and Serianni, A.S., J. Am. Chem. Soc., 1998, vol. 120, p. 11 158; Cloran, F., Carmichael, I., and Serianni, A.S., J. Phys. Chem. A, 1999, vol. 103, p. 3783; Church, T.J., Carmichael, I., and Serianni, A.S., J. Am. Chem. Soc., 1997, vol. 119, p. 8946.
18. Bose, B., Zhao, S., Stenutz, R., Cloran, F., Bondo, P.B., Bondo, G., Hertz, B., Carmichael, I., and Serianni, A.S., J. Am. Chem. Soc., 1998, vol. 120, p. 11 158; Cloran, F., Carmichael, I., and Serianni, A.S., J. Phys. Chem. A, 1999, vol. 103, p. 3783; Church, T.J., Carmichael, I., and Serianni, A.S., J. Am. Chem. Soc., 1997, vol. 119, p. 8946.
19. Grant, D.M., Facelli, J.C., Alderman, D.W., and Sherwood, M.H., Nuclear Magnetic Shieldings and Molecular Structure, Tossell, J.A., Ed., Dordrecht: Kluwer Academic, 1993, p. 367; Barfield, M., Nuclear Magnetic Shieldings and Molecular Structure, Tossell, J.A., Ed., Dordrecht: Kluwer Academic, 1993, p. 523; Liu, F., Phung, C., Alderman, D.W., and Grant, D.M., J. Magn. Reson. Ser. A, 1996, vol. 120, p. 231.
20. Grant, D.M., Facelli, J.C., Alderman, D.W., and Sherwood, M.H., Nuclear Magnetic Shieldings and Molecular Structure, Tossell, J.A., Ed., Dordrecht: Kluwer Academic, 1993, p. 367; Barfield, M., Nuclear Magnetic Shieldings and Molecular Structure, Tossell, J.A., Ed., Dordrecht: Kluwer Academic, 1993, p. 523; Liu, F., Phung, C., Alderman, D.W., and Grant, D.M., J. Magn. Reson. Ser. A, 1996, vol. 120, p. 231.
21. Grant, D.M., Facelli, J.C., Alderman, D.W., and Sherwood, M.H., Nuclear Magnetic Shieldings and Molecular Structure, Tossell, J.A., Ed., Dordrecht: Kluwer Academic, 1993, p. 367; Barfield, M., Nuclear Magnetic Shieldings and Molecular Structure, Tossell, J.A., Ed., Dordrecht: Kluwer Academic, 1993, p. 523; Liu, F., Phung, C., Alderman, D.W., and Grant, D.M., J. Magn. Reson. Ser. A, 1996, vol. 120, p. 231.
22. Cloran, F., Carmichael, I., and Serianni, A.S., J. Am. Chem. Soc., 2000, vol. 122, p. 396.
23. Stenutz, R., Carmichael, I., Wildmalm, G., and Serianni, A.S., J. Org. Chem., 2002, vol. 67, p. 949.
24. Hricovini, M., Malkina, O.L., Bizik, F., Turi Nagy, L., and Malkin, V.G., J. Phys. Chem. A, 1997, vol. 101, p. 9756.
25. Malkina, O.L., Hricovini, M., Bizik, F., and Malkin, V.G., J. Phys. Chem. A, 2001, vol. 105, p. 9188.
26. Krivdin, L.B., Shcherbakov, V.V., and Kalabin, G.A., Zh. Org. Khim., 1986, vol. 22, p. 342.
27. Krivdin, L.B., Zinchenko, S.V., Sherbakov, V.V., Kalabin, G.A., Contreras, R.H., Tufro, M.F., Ruiz De Azua, M.C., and Giribet, C.G., J. Magn. Reson., 1989, vol. 84, p. 1.
28. Cramer, C.J., Truhlar, D.G., and French, A.D., Carbohydr. Res., 1997, vol. 298, p. 1.
29. Gil, V.M.S. and Teixeira-Dias, J.J.C., Mol. Phys., 1968, vol. 15, p. 47; Gil, V.M.S. and Alves, A.C.P., Mol. Phys., 1969, vol. 16, p. 525.
30. Gil, V.M.S. and Teixeira-Dias, J.J.C., Mol. Phys., 1968, vol. 15, p. 47; Gil, V.M.S. and Alves, A.C.P., Mol. Phys., 1969, vol. 16, p. 525.
31. Becke, A.D., J. Chem. Phys., 1993, vol. 98, p. 5648.
32. Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B: Condens. Matter Mater. Phys., 1988, vol. 37, p. 785.
33. Hariharan, P.C. and Pople, J.A., Theor. Chim. Acta, 1973, vol. 28, p. 213.
34. Blizzard, A.C. and Santry, D.P., J. Chem. Phys., 1971, vol. 55, p. 950; Blizzard, A.C. and Santry, D.P., J. Chem. Phys., 1973, vol. 58, p. 4714.
35. Blizzard, A.C. and Santry, D.P., J. Chem. Phys., 1971, vol. 55, p. 950; Blizzard, A.C. and Santry, D.P., J. Chem. Phys., 1973, vol. 58, p. 4714.
36. Coolidge, M.B. and Stewart, J.J.P., QCPE. Program 455 (Release 6.0), 1990.
37. Schmidt, M.W., Baldridge, K.K., Boatz, J.A, Elbert, S.T., Gordon, M.S., Jensen, J.H., Koseki, S., Matsunaga, N., Nguyen, K.A., Su, S.J., Windus, T.L., Dupuis, M., and Montgomery, J.A., J. Comput. Chem., 1993, vol. 14, p. 1347.